Hydrochloric Acid → HCID 58168100, compound

Participants

Reaction Conditions

Reaction Steps

83 (550 mg, 2.17 mmol), methyl 2-(4-aminophenyl)acetate (376 mg, 2.28 mmol), and HCl (0.65 mL, 2.17 mmol, 4.0 M in dioxane) were suspended in NMP (5 mL), and stirred for 3 h at 140° C. The reaction mixture was quenched with saturated aqueous NaHCO3 (100 mL), and stirred for 30 min. The resulting precipitate was filtered, washed with H2O, and dried under vacuum. The methyl ester intermediate (750 mg, 2.09 mmol) and LiOH (150 mg, 6.26 mmol) were dissolved in THF (4 mL) and H2O (4 mL), and stirred for 48 h at room temperature. The THF was removed, the mixture was diluted with H2O, and acidified to pH=5 with 1M HCl. The resulting precipitate was filtered, washed with H2O, and dried under vacuum to provide 302 (550 mg, 76% yield) as a white solid. 1HNMR(DMSO-D6): 3.52(s, 2H), 6.97 (d, 1H), 7.13 (m, 2H), 7.21 (m, 2H), 7.58 (m, 1H), 7.61 (m, 1H)m 8.10 (d, 1H), 8.34(d, 1H), 8.84-8.90 (m, 2H). LC-MS (M+H=346, obsd.=346).

Provenance & Evidence